Travel Guide: Chicago

Travel Guide: Chicago

Last Updated on June 22, 2020 by Laura Cooper

The Windy City will blow you away with its inspiring skyline, music and comedy venues, and ethnic eats. But then you’ll be back for more. That’s Chicago, impressing you at every step. From its cutting-edge architecture to its incredible symphony orchestra, the arts are booming. Fancy a visit? Our Chicago travel guide has everything you need to know for planning a trip to Chicago.

Chicago Skyline

Who should visit Chicago?

Chicago has so much to offer those looking to experience the city: delicious food, varied museums, upscale shopping, some of the best comedy shows, and never-ending sports.

Whether you’re into the Cubs, Bears, Bulls, Blackhawks, or White Sox (or even if you’re just looking for an outing with the family), you can catch a game and cheer along with the fans. Chicago is also known for the arts: whether it be the famous jazz and blues scene, its world-class symphony orchestra, thoughtful or improv comedy shows, and public art on the street. Those interested in architecture can marvel at the buildings and monuments in Chicago, known as the birthplace of the modern day skyscraper.


A great value purchase for a first-time visitor to Chicago, the Go Chicago Card grants you access to over 25 top Chicago attractions like the rides at Navy Pier, Shedd Aquarium, and SkyDeck Chicago. Cards can be purchased for one, two, three, or five consecutive days and allows you to create your own itinerary with great savings. Another option is the Chicago City Pass which gives you admission to five attractions including the Shedd Aquarium, Field Museum, Skydeck Chicago, Choice 1 (Museum of Science OR 360 Chicago) and Choice 2 (Adler Planetarium OR Art Institute of Chicago).

Grant Park

Chicago City Tour and River Cruise: Get acquainted with the city from land and water with a narrated coach tour to see Grant Park, the Loop, the Shedd Aquarium, and popular neighbourhoods before cruising along the Chicago River in a yacht to admire the skyline. If just a cruise sounds appealing, the Chicago Sunset Dinner Cruise includes a buffet dinner, dancing, and sightseeing on a three-hour luxury cruise on Lake Michigan. Additional Chicago cruises like architecture cruises or speedboat rides are also available.

Below are some notable attractions you may want to add to your list of places to visit in Chicago. Sightseeing tickets and passes can be purchased in advance.


Field Museum: Home to the largest Tyrannosaurus rex fossil ever found, mummies in the Ancient Egypt exhibit and over 26 million biological specimens and cultural artifacts, this natural history museum has much to be discovered.

Adler Planetarium: America’s first planetarium, the Adler features full-sized theatres and telescopes, and exhibits like the hands-on Community Design Lab Mission Moon where you can learn what it’s like to be an astronaut, and The Universe where you can walk through space and time.

John G. Shedd Aquarium: Explore this indoor aquarium and enjoy extraordinary experiences like the aquatic show, petting stingrays and penguins, and spotting animals like beluga whales, sea lions, and dolphins.

Museum of Science and Industry: See science come alive with interactive exhibits and experiences. Discover mathematical patterns in nature, interact with robots, feel the physics of natural disasters, and more.

Frank Lloyd Wright Home and Studio: Visit the private residence and workplace of Wright where he experimented with design elements from 1889-1909, the first 20 years of his career.

Chicago Art Institute

Chicago Art Institute: Housing both an impressionist collection and modern art gallery, the Chicago Art Institute features photography, textiles, sculpture, and more.

Museum of Contemporary Art: Spend some time admiring the painting, sculpture, photography, video, film, and performance in this downtown Chicago museum.

Robie House: This National Historic Landmark on the Chicago University campus was created by Frank Lloyd Wright for his client, Frederick Robie. The house is known as an icon of modern architecture.

National Museum of Mexican Art: Showcasing 3000 years of Mexican culture, this 7,500 piece permanent collection immerses you into Mexican art and identity.


Millennium Park: This is the spot for strolling, people watching, and gathering by the lakefront. Visit the 110-tonne Cloud Gate sculpture that resembles a silver-drop, or the Pritzker Music Pavilion band shell, host to free concerts in the summertime.

Millennium Park

360 Chicago (formerly John Hancock Observatory): Experience views of the iconic cityscape from Chicago’s third tallest building located along Magnificent Mile.

Magnificent Mile: This 14 block stretch is home to shopping, hotels, dining, spas, and attractions like museums and theatres. People visit for the designer boutiques and high-end malls or to stroll along and people watch. (Bucktown and Armitage Avenue are also shopping hot-spots.)

Fashion Outlets of Chicago: Located just five minutes from the O’Hare Airport and 15 minutes from downtown Chicago, this two-level indoor shopping mall features over 130 outlets plus dining options for visitors to get their shopping fix and save. You’ll find luxury department stores like Bloomingdale’s and Saks Fifth Avenue as well as affordable brands like Forever 21 and J.Crew mixed with higher-end labels like Gucci and Prada. View the voucher for savings.

Wrigley Field: Catch a game at this famous Major League Baseball field, built in 1914.

Willis Tower: Formerly known as the Sears tower, the Willis Tower is home to thriving businesses and is a landmark seen from all ends of the city.

Navy Pier

Navy Pier: With entertainment, dining, parks, cruises, and events, The Navy Pier was opened in 1916 and offers lovely views of downtown and carousel rides for kids.

Chinatown: On the South Side of Chicago lies the ethnic neighbourhood of Chinatown, the second largest in North America. Chinatown Gate leads to Chinatown Square, the main area with vibrant shops and restaurants.

Lincoln Park Zoo: Open year-round, this free attraction is a great way to spend a day with the family in Chicago.

Lincoln Park


Second City Theater: Opening its doors in 1959, Second City has grown into a recognizable comedy theatre around the world. Stop by for a unique performance of improv and comedy.

Tommy Gun’s Garage Dinner and Show: This dinner-show will transport you to the roaring ’20s to be entertained by gangsters and flappers.

Buckingham Fountain: This Chicago landmark was built in 1927 and stands in the center of Grand Park.

Buckingham Fountain

Boys Town: Chicago is a very LGTBQ friendly city, particularly the area referred to as Boys Town on the North Side, where you’ll find fabulous bars, restaurants, and things to do like shopping, comedy shows, and theatre.

Helicopter Tour: See the famous Chicago skyline from up high on an exciting helicopter tour.

Beaches: Locals and tourists visit North Avenue Beach, a popular spot in the summer, to enjoy volleyball games and making sandcastles. The sandy Oak Street Beach is also a go-to with lots of kids and bike-riders enjoying the sunshine. Both beaches have cold waters so don’t plan on swimming in Lake Michigan.


Food and Drinks

Deep-dish pizza, loaded hot dogs, and Italian beef sandwiches are the quintessential Chicago treats to try while you’re there. With so much culinary and cultural diversity, and a booming Greektown, China Town, and Little Italy, almost any craving can be satisfied.

Food, wine and nightlife tours are available such as pizza and beer tours and a Chicago prohibition tour.


  • Alinea: If you’re looking to splurge and experience an unconventional dinner, this is your place. Featuring 18-22 tasting menu options, Alinea provides beautifully presented, gourmet cuisine.
  • Everest: Providing the best views from the 40th floor of the Stock Exchange, Everest cooks up French cuisine at its finest and boasts a selection of over 1,600 wines.
  • Gene & Georgetti: This family-owned steakhouse opened in 1941 and serves up a lunch and dinner menu.
  • MK: Taste owner and Chef Michael Kornick’s American food using seasonal ingredients in a dimly, lit and elegant exposed-brick setting.
  • North Pond: Enjoy romantic and seasonal food at the elegant North Pond, overlooking a pond on the Lincoln Park grounds.
  • Avec: This trendy restaurant features European wines, artisanal cheeses, tapas and main courses with communal seating.
  • Blackbird: Dine in for a Mediterranean-inspired dish made from local produce.

Pizza: Try Chicago’s legendary deep dish pizza with the family at Gino’s East of Chicago or Lou Malnati’s Pizzeria.


Chicago Neighbourhood

The Loop district is the business and tourist district in the heart of downtown Chicago with skyscrapers and public art attracting people to its core. It is a pricier, but more convenient place to stay, close to major sights like Millennium Park, the Field Museum, Adler Planetarium, Willis Tower, Art Institute of Chicago, Chicago Theatre, and more.

River North is the second most popular place to stay in Chicago, known for its trendy art galleries, restaurants, and nightlife. It is home to the “Magnificent Mile” shopping and hotel district along Michigan Avenue.

The West side of the Loop is less touristy and home to diverse neighbourhoods like Greektown, Chinatown, and Little Italy. It is home to some of the city’s best restaurants and happening shops and bars. Uptown Chicago is an artsy and laid-back district, with residential spaces, beaches, and entertainment venues like jazz clubs and theatres.

In the Loop

Trump Tower

Hotel Blake, 3-star Housed in a 19th century building, Hotel Blake has a historic exterior but chic design inside. This pet-friendly hotel is equipped with a 24-hour fitness center and business center, Meli Café onsite restaurant, and room service.

Hard Rock Chicago, 4-star: Close to Millennium Park, the Art Institute of Chicago, Magnificent Mile, and the Navy Pier, the pet-friendly Hard Rock Chicago boasts two fantastic restaurants plus room service if you’re just looking to relax, a gym, and contemporary accommodations.

On Magnificent Mile

Westin Michigan Avenue, 4-star: Set on Magnificent Mile, guests can enjoy attractions along the avenue and strolls along Navy Pier. The hotel has 752 guest rooms, a fitness studio, spa, grill restaurant, and café.

The Peninsula Chicago, 4.5-star: Embodying romance and luxury, the elegant rooms, wellness spa, outdoor terrace, and indoor pool will impress.

The James Hotel, 4-star: This boutique hotel is just steps from Michigan Avenue’s Magnificent Mile, close to shopping, dining, and nightlife options and within walking distance of attractions like Millennium Park and The Museum of Contemporary Art. The hotel is celebrated for its steakhouse and craft cocktail lounge as well as its meeting and event space.

Park Hyatt Chicago, 4.5-star: Offering great views of the city, this sophisticated hotel is located within three blocks of the shopping of Magnificent Mile, Millennium Park, the Loop business district, Wrigley Building, and the Theatre District. On-site, you’ll find a relaxing spa, indoor pool, cocktail lounge, and rooftop bar and restaurant.

North River

Hotel Chicago, An Autograph Collection Hotel, 4-star: In the heart of the River North neighbourhod, Hotel Chicago is across from the famous House of Blues and features the in-house Chicagoan restaurant.

W Chicago Lakeshore, 4-star: This sleek pet-friendly hotel towers over Lake Michigan with its glamorous rooms, Bliss spa, gym, Wired business center, and a Wet Deck pool bar on the 7th floor – all just steps from the Navy Pier and Magnificent Mile.

When to go and for how long?


Summer is peak season in Chicago when temperatures average 26-34C, bringing more crowds and higher prices. Spring and fall have warm weather with fall seeing temperatures start off around 21C and cooling down to around 7C and springtime averaging 15C and heating up to around 21C, with fair amounts of rain. Wintertime sees average snowfall of 37 inches and daily highs from -1C to 3C. The weather can be cold, but the city offers better prices and no line ups at museums and attractions during the winter season.

We recommend booking a hotel in advance, especially if you’re travelling during busy season. Chicago hosts many festivals including:

  • Chicago Chinese New Year Parade: End of January
  • Chicago Underground Film Festival – March
  • St Patrick’s Day Parade- March
  • Gay Pride Parade- March
  • Taste of Chicago – July
  • Lollapalooza– August
  • Chicago Jazz Festival – August/September
  • Chicago Marathon – October
  • Chicago International Film Festival – October

Most people visit Chicago for just a weekend, but even a whole week can be spent exploring all the city has to offer.

Travel Style

Most people arrange their Chicago vacation by booking their flights and hotels separately, and later arranging their day trips. Our vacation packages can make it easier by combining both into one bundle with a range of hotels to choose from. Other people choose to arrange a tour of Chicago with stops along the way, such as visits to New Orleans, Memphis, or Los Angeles.

Getting There

Aerial View

The O’Hare International airport is 27km northwest of downtown, and is one of the largest airports in the world. It is more popular than the Midway International Airport, which is only 16km from downtown.

Flights to Chicago from Toronto take approximately two hours while flights from Vancouver take four. The drive from O’Hare airport to the downtown core can take 30 minutes to over an hour depending on traffic. You can reach the city center via public transportation from the airport. The metro costs approximately $5 and takes 45 minutes, while a taxi would cost around $40. Airport transfers are also available.

Getting Around

LaSalle Street

There is no need to rent a car in Chicago as most of the main attractions are within walking distance or on public transportation routes. Chicago is a walkable city with grid-like streets that are easy to navigate.

The Chicago Transit Authority (CTA) is the public transportation system. The bus system is comprised of 140 routes while the CTA “L” train service, the city’s metro system, has eight routes and 146 stations.

A full “L” train fare is $2.25 while a bus fare is $2.00. A one-day pass loaded onto the Ventra transit account (the reloadable pass card) is $10 and a 3-day pass is $20.

The Chicago City Hop-on Hop-off Tour is a convenient way to get around for first-time visitors looking for a good overview of the city. See the sights at your own pace, hopping off the double-decker bus at any of the 12 stops.

Walking and biking tours are also available. For the more active and adventurous type, the Chicago Segway Tour takes you to famous sights like the Buckingham Fountain, Navy Pier, and more as you glide along.


Flights range from $330 to $800 round-trip depending on your departure city. Weekend getaways including both flights and hotels can range from $430 to $900. Hotels range from $89 per night to $500+, comparable to other North American hotels.


  1. I can see myself exploring Chicago.!!

  2. How nice to get away and visit someplace you have always heard of, but never visited. What a great prize at Christmas time. Way to go Trip Trivia.

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